Molecular self assembly of benzene-1,3,5-tricarbonyl phenylalanine

Benzene-1,3,5-tricarboxylic acid derivatives with amino acids have a strong tendency to aggregate in solution. In the present communication we report a detailed study of the self assembly of these derivatives containing Phe and Val. Intermolecular hydrogen bonding, π⋯π and weak C–H⋯X (X = π, O, N) interactions are involved in the process of molecular assembly.

► TMA derivatives of Phe (2) and Val (3) were studied by NMR, X-ray, TEM and MASS.
► Central aromatic rings in 2 display edge to edge inter-molecular interaction.
► Intermolecular H-bonding, π⋯π and C–H⋯X (π, O, N) interactions support assembly.
► In 2, small crystals are seen at low concentration and fibrils at high concentration.